US5306706A - Perfume bases - Google Patents

Perfume bases Download PDF

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US5306706A
US5306706A US07/956,023 US95602392A US5306706A US 5306706 A US5306706 A US 5306706A US 95602392 A US95602392 A US 95602392A US 5306706 A US5306706 A US 5306706A
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Prior art keywords
usnic acid
benzyl
raw material
perfume
pct
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US07/956,023
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Ahmet E. Baydar
Ghislaine-Henriette Caylus
Christof B. Selden
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Givaudan Roure Corp
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Givaudan Roure Corp
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Assigned to GIVAUDAN-ROURE (INTERNATIONAL) S.A. reassignment GIVAUDAN-ROURE (INTERNATIONAL) S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYDAR, AHMET ENNIS, CAYLUS, GHISLAINE-HENRIETTE, SELDEN, CHRISTOF BASTIAN
Assigned to GIVAUDAN-ROURE CORPORATION reassignment GIVAUDAN-ROURE CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GIVAUDAN-ROURE (INTERNATIONAL) S.A.
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom

Definitions

  • Usnic acid a natural well-known antimicrobial agent, has been demonstrated to be extremely effective against Gram-positive bacteria, fungi, and yeast with Minimum Inhibitory Concentrations as low as 10 ppm for certain species [M. Fontana, G. Proserpio, Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (RIPOAM), 1974, 56, 315-336].
  • the use of free usnic acid in cosmetic formulations is complicated due to its insolubility in all commonly used solvent systems [H. Bergerhausen, Cosmetics and Toiletries 1976, 91, 25-26; Manufacturing Chemist 1989, 22-27].
  • Soluble derivatives of usnic acid such as its alkali and ammonium salts, as well as certain esters, have been reported [Handelsgesellschaft Schlosser GmbH, 1975, Ger. Offen. 2354517. Orissa Drebing GmbH, 1975, Ger. Offen. 2351927. Orissa Drebing GmbH, 1975, Ger. Offen. 2351864. Orissa Drebing GmbH, 1976, Ger. Offen. 2432484.].
  • the major drawbacks of these derivatives are their insufficient stability properties, such as decolorization, pH-sensitivity, and reduction of antimicrobial activity.
  • Solubility at 25° C. water ⁇ 0.01, acetone 0.77, ethyl acetate 0.88, ethanol 0.02, chloroform 4.6, pyridine 2.12, benzene 0.94, dioxane 0.99, isopropyl alcohol 0.28, propylene glycol ⁇ 0.01, dipropylene glycol 0.01, diethyl phthalate 0.45.
  • benzyl salicylate (1), benzyl benzoate (2), anisic aldehyde (3), isoeugenol methylether (4), cinnamyl acetate (5), and eugenol (6).
  • perfumery raw materials exhibiting the desired solubilizing property are thus not only odorants, but also fixatives, blenders and modifiers.
  • benzyl salicylate 3.01, benzyl benzoate 1.93, anisic aldehyde 4.06, isoeugenol methylether 2.69, cinnamyl acetate 1.60, eugenol 2.18, anethol 4.30.
  • Perfume compositions containing free usnic acid can thus be readily incorporated in the usual manner and using the well-known techniques into perfumed consumer products, e.g. into a wide variety of cosmetic and toiletry formulations, such as deodorants, antiperspirants, shower gels, soaps, sanitary pads, skin creams, lotions, tooth paste, mouth wash, etc.
  • Such tooth paste may contain the usual ingredients such as abrasives, surfactants, humectants, binders, therapeutic ingredient(s), if necessary, anti tartar ingredients, preservatives, whiteners, etc.
  • Fragrance Formula 1 may contain for example 0,80 parts and 3,00 parts per weight, respectively, of Fragrance Formula 1 (or 2, or 3)
  • the usnic acid in anethol is conveniently ca. 1.5 to 2.5% per weight.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials For Medical Uses (AREA)
  • Prostheses (AREA)
  • Surgical Instruments (AREA)

Abstract

PCT No. PCT/EP92/00823 Sec. 371 Date Dec. 7, 1993 Sec. 102(e) Date Dec. 7, 1993 PCT Filed Apr. 11, 1992 PCT Pub. No. WO92/18097 PCT Pub. Date Oct. 29, 1992.Perfume base, containing usnic acid and a perfumery raw material exhibiting an aromatic ring.

Description

Usnic acid, a natural well-known antimicrobial agent, has been demonstrated to be extremely effective against Gram-positive bacteria, fungi, and yeast with Minimum Inhibitory Concentrations as low as 10 ppm for certain species [M. Fontana, G. Proserpio, Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (RIPOAM), 1974, 56, 315-336]. The use of free usnic acid in cosmetic formulations is complicated due to its insolubility in all commonly used solvent systems [H. Bergerhausen, Cosmetics and Toiletries 1976, 91, 25-26; Manufacturing Chemist 1989, 22-27]. Soluble derivatives of usnic acid, such as its alkali and ammonium salts, as well as certain esters, have been reported [Handelsgesellschaft Schlosser GmbH, 1975, Ger. Offen. 2354517. Orissa Drebing GmbH, 1975, Ger. Offen. 2351927. Orissa Drebing GmbH, 1975, Ger. Offen. 2351864. Orissa Drebing GmbH, 1976, Ger. Offen. 2432484.]. The major drawbacks of these derivatives are their insufficient stability properties, such as decolorization, pH-sensitivity, and reduction of antimicrobial activity.
Usnic acid [C18 H16 O7, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione] exhibits the following characteristics:
MW 344.32; mp 201°-203° C., [α]D +488° (c 0.4,CHCl3);mp 204° C.,[α]D +509.4° (c0.697,CHCl3);
Solubility at 25° C. (g/100 ml): water<0.01, acetone 0.77, ethyl acetate 0.88, ethanol 0.02, chloroform 4.6, pyridine 2.12, benzene 0.94, dioxane 0.99, isopropyl alcohol 0.28, propylene glycol<0.01, dipropylene glycol 0.01, diethyl phthalate 0.45.
Certain perfumery raw materials now have been found to solubilize usnic acid--and leading to stable solutions. This finding allows the direct use of usnic acid, this natural antimicrobial agent isolated from alpine lichen, in numerous types of perfumes, cosmetic and toiletry formulations, without the usually required derivatization to improve its solubility.
The natural and synthetic perfumery raw materials are all characterized by exhibiting an aromatic ring. In the foreground of the interest are such standard perfumery materials as:
benzyl salicylate (1), benzyl benzoate (2), anisic aldehyde (3), isoeugenol methylether (4), cinnamyl acetate (5), and eugenol (6).
These perfumery raw materials exhibiting the desired solubilizing property are thus not only odorants, but also fixatives, blenders and modifiers.
The amount of any of (1) to (6) in the perfume bases is not too critical. Convenient amounts are:
about 20 to about 90% of any of (1) to (6). Mixtures of any one of (1) to (6) are also possible.
The maximum solubility (g/100 ml) of pure usnic acid in the above pure compounds (1) to (6) at 25° C. is:
benzyl salicylate 3.01, benzyl benzoate 1.93, anisic aldehyde 4.06, isoeugenol methylether 2.69, cinnamyl acetate 1.60, eugenol 2.18, anethol 4.30.
EXAMPLES
Three formulae of perfume compositions containing different concentrations of free usnic acid are listed below:
______________________________________                                    
Formula 1.                                                                
Compound                wt. %                                             
______________________________________                                    
Usnic Acid              0.5                                               
1                       20.0                                              
2                       18.0                                              
6                       2.0                                               
Linalool                8.0                                               
Benzyl Acetate          8.0                                               
Hexyl Cinnamic Aldehyde 13.5                                              
Phenyl Ethyl Alcohol    2.0                                               
Hydroxycitronellal      4.0                                               
Ylang Ylang Oil         2.0                                               
Aldehyde C-14           6.0                                               
Aldehyde C-18           6.0                                               
Methyl Anthranilate     4.0                                               
Indolene-50 [8,8-bis-(3H-indol-3-yl)-2,6-                                 
                        2.0                                               
dimethyl-2-octanal 50% in castor oil]                                     
Methyl Salicylate       4.0                                               
                        100.00                                            
______________________________________                                    

______________________________________                                    
Formula 2.                                                                
Compound              wt. %                                               
______________________________________                                    
Usnic Acid            1.50                                                
1                     70.0                                                
2                     7.0                                                 
4                     0.30                                                
Linalool              1.00                                                
Benzyl Acetate        7.00                                                
Linalyl Acetate       0.70                                                
Hexyl Cinnamic Aldehyde                                                   
                      2.30                                                
Phenyl Ethyl Alcohol  3.00                                                
Hydroxycitronellal    5.70                                                
Geraniol Extra        0.30                                                
Cinnamic Alcohol      0.15                                                
Aldehyde C-14 (10% in DEP)                                                
                      0.15                                                
Aldehyde C-16 (10% in DEP)                                                
                      0.15                                                
Aldehyde C-18 (10% in DEP)                                                
                      0.30                                                
Argeol [hydroxycitronellal-methyl                                         
                      0.15                                                
anthranilate Schiff base]                                                 
α-Ionone        0.30                                                
                      100.00                                              
______________________________________                                    

______________________________________                                    
Formula 3.                                                                
Compound                wt. %                                             
______________________________________                                    
Usnic Acid              2.00                                              
1                       85.0                                              
2                       0.80                                              
6                       0.20                                              
Linalool                0.80                                              
Phenyl Ethyl Alcohol    6.70                                              
Geraniol Extra          0.90                                              
Citronellol Extra       0.90                                              
Geranyl Acetate         0.90                                              
Phenyl Aethyl Acetate   0.80                                              
Diphenyl Oxide (10% in DEP)                                               
                        0.01                                              
Aldehyde C-9 (10% in DEP)                                                 
                        0.02                                              
Aldehyde C-18 (10% in DEP)                                                
                        0.02                                              
Methyl Ionantheme-100 [α-methyl ionone]                             
                        0.02                                              
(10% in DEP)                                                              
Iso Menthone (10% in DEP)                                                 
                        0.08                                              
Rose Oxide (10% in DEP) 0.04                                              
Methyl Octine Carbonate (10% in DEP)                                      
                        0.01                                              
Phenyl Aethyl Phenyl Acetate                                              
                        0.80                                              
                        100.00                                            
______________________________________
Perfume compositions containing free usnic acid can thus be readily incorporated in the usual manner and using the well-known techniques into perfumed consumer products, e.g. into a wide variety of cosmetic and toiletry formulations, such as deodorants, antiperspirants, shower gels, soaps, sanitary pads, skin creams, lotions, tooth paste, mouth wash, etc. Such tooth paste may contain the usual ingredients such as abrasives, surfactants, humectants, binders, therapeutic ingredient(s), if necessary, anti tartar ingredients, preservatives, whiteners, etc.
Two example formulations of applications in a deodorant stick and a deodorant non-aerosol spray are given below.
______________________________________                                    
Deodorant Stick:                                                          
______________________________________                                    
Propylene glycol         63.00%                                           
Sodium stearate          5.00%                                            
Deionized water          25.00%                                           
Hydroxyethylcellulose (Natrosol 250)                                      
                         0.20%                                            
Isostearamidopropyl PG diethyl ammonium                                   
                         2.00%                                            
chloride (Lexquat AMG-IS)                                                 
Lauramide DEA (Standamid LD>)                                             
                         4.00%                                            
Formula 1 (or 2, or 3)   0.80%                                            
                         100.00%                                          
______________________________________                                    

______________________________________                                    
Non-Aerosol Deodorant Spray:                                              
______________________________________                                    
Propylene glycol     3.00%                                                
Water                20.50%                                               
Ethanol              75.00%                                               
Formula 1 (or 2, or 3)                                                    
                     1.50%                                                
                     100.00%                                              
______________________________________
Shower gel:
Conventional shower gels, such as described in
Cosmetic & Toiletries 104 (1989), 84 seq., in particular 86, or in
Cosmetic & Toiletries 99 (1984) 96
may contain for example 0,80 parts and 3,00 parts per weight, respectively, of Fragrance Formula 1 (or 2, or 3)
______________________________________                                    
Tooth paste:                                                              
______________________________________                                    
Calcium carbonate    50.00%                                               
Sodium lauryl sulphate                                                    
                     1.50%                                                
Glycerol             10.00%                                               
Sorbitol             15.00%                                               
Gum tragacanth       1.50%                                                
Sodium monofluorophosphate                                                
                     0.90%                                                
Tetrasodium pyrophosphate                                                 
                     0.25%                                                
Zinc citrate trihydrate                                                   
                     0.50%                                                
Saccharin            0.10%                                                
Formaldehyde (40%)   0.06%                                                
anethol based perfume or flavour                                          
                     1.00%                                                
Water to             100.00%                                              
______________________________________
The usnic acid in anethol is conveniently ca. 1.5 to 2.5% per weight.

Claims (6)

We claim:
1. Perfume base, comprising usnic acid in combination with a perfumery raw material, which is selected from the group consisting of benzyl salicylate, benzyl benzoate, anisic aldehyde, isoeugenol methylether, cinnamyl acetate, eugenol and anethol, the concentration of usnic acid being from about 0.3% w/w to about 3% w/w.
2. Perfume base according to claim 1, wherein the perfumery raw material is selected from the group consisting of benzyl salicylate, benzyl benzoate, anisic aldehyde, isoeugenol methylether, cinnamyl acetate and eugenol.
3. A method for improving the solubility of usnic acid in a perfume composition which comprises incorporating into said perfume composition a perfumery raw material which is selected from the group consisting of benzyl salicylate, benzyl benzoate, anisic aldehyde, isoeugenol methylether, cinnamyl acetate, eugenol and anethol, and wherein the usnic acid is employed in a concentration from about 0.3% w/w to about 3% w/w.
4. The method according to claim 3 wherein the perfumery raw material is selected from the group consisting of benzyl salicylate, benzyl benzoate, anisic aldehyde, isoeugenol methylether, cinnamyl acetate and eugenol.
5. Perfume base according to claim 1 wherein the concentration of usnic acid is about 0.5% w/w to about 2% w/w.
6. The method according to claim 3 wherein the concentration of usnic acid in said perfume composition is about 0.5% w/w to about 2% w/w.
US07/956,023 1991-04-20 1992-04-11 Perfume bases Expired - Fee Related US5306706A (en)

Applications Claiming Priority (3)

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EP91106402 1991-04-20
EP91106402.0 1991-04-20
PCT/EP1992/000823 WO1992018097A1 (en) 1991-04-20 1992-04-11 Perfume bases

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EP (1) EP0535195B1 (en)
JP (1) JPH05508182A (en)
CA (1) CA2085892C (en)
DE (1) DE69201230T2 (en)
ES (1) ES2067333T3 (en)
WO (1) WO1992018097A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999019433A1 (en) * 1997-10-10 1999-04-22 Avon Products, Inc. Shower and shave body wash
US20030105439A1 (en) * 2001-10-02 2003-06-05 Kimberly-Clark Worldwide, Inc. Inhibition of exoprotein production in absorbent articles using isoprenoids

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69232292T2 (en) * 1992-01-24 2002-08-22 Gillette Co USNIC ACID IN A DEODORANT PEN
CA2214675C (en) * 1995-03-07 2008-12-23 New Zealand Institute For Crop & Food Research Limited Methods and compositions for sedating, anaesthetising and euthanising aquatic organisms
US20050152858A1 (en) * 2003-07-11 2005-07-14 Isp Investments Inc. Solubilizing agents for active or functional organic compounds
GB0919210D0 (en) * 2009-11-03 2009-12-16 Syntopix Ltd Formulations

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2341927A1 (en) * 1973-08-20 1975-03-27 Bosch Gmbh Robert BATTERY CHARGER
DE2351864A1 (en) * 1973-10-16 1975-04-24 Orissa Drebing Gmbh Antibacterial deodorising cosmetic compsn - contains a lichen acid, a solvent aid and a solvent
DE2354517A1 (en) * 1973-10-31 1975-05-28 Handelsgesellschaft Schlosser Skin cosmetics e.g. deodorant sprays - contg. lichen acids, pref. usnic or evernic acids, dissolved in alcohols with hydroxy-amines
DE2432484A1 (en) * 1974-07-04 1976-01-22 Orissa Drebing Gmbh COSMETIC AGENT

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2351927A1 (en) * 1973-10-16 1975-04-24 Orissa Drebing Gmbh Deodorising cosmetic compsns. - contg. lichen acid derivs, have enhanced antimicrobial activity

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2341927A1 (en) * 1973-08-20 1975-03-27 Bosch Gmbh Robert BATTERY CHARGER
DE2351864A1 (en) * 1973-10-16 1975-04-24 Orissa Drebing Gmbh Antibacterial deodorising cosmetic compsn - contains a lichen acid, a solvent aid and a solvent
DE2354517A1 (en) * 1973-10-31 1975-05-28 Handelsgesellschaft Schlosser Skin cosmetics e.g. deodorant sprays - contg. lichen acids, pref. usnic or evernic acids, dissolved in alcohols with hydroxy-amines
DE2432484A1 (en) * 1974-07-04 1976-01-22 Orissa Drebing Gmbh COSMETIC AGENT

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
H. Bergerhausen, Cosmetics and Toiletries, 91 (1976) 25 26. *
H. Bergerhausen, Cosmetics and Toiletries, 91 (1976) 25-26.
Inoue et al, Chem. Abst., vol. 93, #88,256s (1980).
Inoue et al, Chem. Abst., vol. 93, 88,256s (1980). *
M. Fontana et al., Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (1974), 56, 315 336. *
M. Fontana et al., Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (1974), 56, 315-336.
Manufacturing Chemist, Oct. 1989, 22 27. *
Manufacturing Chemist, Oct. 1989, 22-27.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999019433A1 (en) * 1997-10-10 1999-04-22 Avon Products, Inc. Shower and shave body wash
US5902779A (en) * 1997-10-10 1999-05-11 Avon Products, Inc. Shower and shave body wash
US20030105439A1 (en) * 2001-10-02 2003-06-05 Kimberly-Clark Worldwide, Inc. Inhibition of exoprotein production in absorbent articles using isoprenoids
US8084046B2 (en) * 2001-10-02 2011-12-27 Kimberly-Clark Worldwide, Inc. Inhibition of exoprotein production in absorbent articles using isoprenoids

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DE69201230T2 (en) 1995-08-10
WO1992018097A1 (en) 1992-10-29
CA2085892C (en) 2002-12-10
ES2067333T3 (en) 1995-03-16
CA2085892A1 (en) 1992-10-21
EP0535195A1 (en) 1993-04-07
EP0535195B1 (en) 1995-01-18
DE69201230D1 (en) 1995-03-02
JPH05508182A (en) 1993-11-18

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